The Roaring ‘20s is known for speakeasies, mobsters and prohibition. Fitting, then, that the original location of interactive dinner show Tommy Gun’s Garage was a 1920s shooting range.

Though the venue moved to its current 6,000-square-foot South Loop spot in 2004, this neighborhood also used to be a wellknown area to drink illegal hooch.

“We wanted to bring a part of Chicago history back. It was a fun time as well as a dangerous time,” says Sandy Mangen, president. The theme continues with the staffers that dress as gangsters and flappers, and interact in character throughout the night.

Tommy Gun’s can host 193 people for a seated event, which can include an Italianstyle feast (with lasagna, roasted prime rib, and fried ravioli) as well as the musical comedy sketch. Planners also have the option of bringing in their own food for private functions, which can be expanded to 250 with a cocktail setup.

In 2009, Keene Addington had just sold his restaurant chain and decided to embark on a road trip around the U.S. While exploring the country, he realized what he wanted to do next—create an authentic 1940s-inspired supper club. Opened in 2012 in River North, Tortoise Cub really brings the stylish decade to life.

“I told the interior designer one thing: Create a room for me where I could picture Dean Martin and Frank Sinatra drinking a brandy and smoking a cigar,” recalls Addington.

That idea turned into the Red Room, which can accommodate 60 people. The restaurant’s main private dining space, The Clubhouse, can accommodate 115 depending on the layout. It’s located in the heart of the restaurant and overlooks the dining room. Addington says that 90 percent of the time groups leave the shades open—perhaps to see what everyone else is eating. Delicious dishes include chicken liver mousse and crab cakes for starters and Chilean sea bass and buttermilk fried Cornish game hen (in addition to traditional chops) for mains.

Addington believes the reason Tortoise Club stands out is for its family ownership, with either him or his wife there at all times. “When the owner is on-site, there is always going to be more attention to detail,” he says. “When you walk into this restaurant, you feel this elegance, sophistication and warmth.”

“Mad Men” may have ended, but that doesn’t mean the show’s impact on today’s pop culture hasn’t stuck around. The idea of business lunches with stiff drinks is still very much alive at places like Pomp and Circumstance in Chicago’s Old Town neighborhood. “We do really great old-fashioneds and your typical comfort food,” says Director of Events Brigette Valliant. Some tasty items include bacon dates, pot roast, smoked rainbow trout and drunken mussels.

The restaurant has two areas for special events. The crown jewel is a year-round private garden patio with space for 30 to 50, depending on setup. It has a retractable room and floral and plants that climb up the wall. Valliant calls it “Alice in Wonderland meets The Secret Garden.”

The second space, on the top floor, is called The Bar Above. It has a maximum capacity of 125, reception-style, and a separate lounge space for 50 guests.

Though the best part of Pomp and Circumstance’s event offerings might be the interactive options like make-your-own sundae bars, working mixologists and, in a classic nod to the decade, an old-fashioned cart.

Pac-Man is one of the most instantly recognizable gaming characters of all time—he’s also an iconic figure of the 1980s.

The ongoing popularity inspired Namco, Pac-Man’s developer, to create a restaurant in Schaumburg dedicated solely to the game, naming it after the highest level you can reach.

“They wanted to create a space reminding adults that it’s okay to play at any age,” says Meghan Reaney, group and event sales manager, “and [to provide] a restaurant that has good food and drinks, and fun entertainment options, all under one roof.”

The 42,000-square-foot venue in Woodfield Mall has a little more than 4,000 square feet of private event space, which can hold up to 335 people. A full buyout is also possible for 700. Décor includes chandeliers, garage doors that open to the outside and mirrored tiles.

Of course there’s also myriad arcade games, bowling lanes and board games as well as two 84-inch LED interactive touchscreen projectors for business needs. Everything is customizable, including menus, which offer shrimp spring rolls and BBQ pulled pork nachos, sushi, salad, pizza, pasta, sandwiches, and mains like risotto and bacon apple pork chops.

Tom Cruise would be proud of this Wicker Park bar that opened in January, named in homage to one of the actor’s most famous roles in Risky Business. The movie kicked off a special viewing series, and is just one part of the plan for upcoming specials to draw in a crowd.

They won’t have much work to do with all the treasured mementoes decorating the spot, though, including leg lamps from A Christmas Story and Teenage Mutant Ninja Turtle lunchboxes. Original cocktails even get in on the fun with names like Drew Berrie’s N’ More and Champagne Supernova.

“The owner [Chris Johnston of CPG Restaurant Group] grew up in that age and wanted to make a bar that [reflects that time],” says Katie Johnson, event coordinator for CPG. “There are subtle, nostalgic pieces all around.”

Though Johnston’s vision was to create a bar dedicated to fries, much like his first restaurant Cheesie’s is all about grilled cheese, the menu has expanded to include three-bean chili and jambalaya, salads, burgers stuffed with mac and cheese and crab cakes, as well as desserts like pumpkin crème brûlée made with Fireball whiskey.

One of the best features of Whiskey Business is its rooftop—the only one in the Wicker Park area. Approximately 250 people can fit on the roof when connected with a second-floor indoor area. The main floor welcomes an additional 95 guests.